A highly enantioselective asymmetric hydrogenation route to β-(2R,3S)-methyltryptophan

被引：38

作者：

Hoerrner, RS ^{[1
]}

Askin, D ^{[1
]}

Volante, RP ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(98)00604-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric hydrogenation of a protected (Z)-dehydro-beta-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97 % ee. Deprotection then afforded (2R,3S)-beta-methyltryptophan 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3455 / 3458

页数：4

共 23 条

[1] Enantioselective catalytic hydrogenation
Albrecht, J
Nagel, U
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04): : 407 - 409
[2] BETA-CARBOLINES DERIVED FROM BETA-METHYLTRYPTOPHAN AND A STEREOSELECTIVE SYNTHESIS OF 2RS,3SR)-BETA-METHYLTRYPTOPHAN METHYL-ESTER
BEHFOROUZ, M
ZARRINMAYEH, H
OGLE, ME
RIEHLE, TJ
BELL, FW
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (06) : 1627 - 1632
[3] THE SYNTHESIS OF 4-SUBSTITUTED INDOLES VIA ARENETRICARBONYLCHROMIUM(O) COMPLEXES
BESWICK, PJ
GREENWOOD, CS
MOWLEM, TJ
NECHVATAL, G
WIDDOWSON, DA
[J]. TETRAHEDRON, 1988, 44 (23) : 7325 - 7334
[4] BOCCHI V, 1982, SYNTHESIS-STUTTGART, P1096
[5] ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF OPTICALLY PURE ISOMERS OF N-INDOLE-(2-MESITYLENESULFONYL)-BETA-METHYLTRYPTOPHAN
BOTEJU, LW
WEGNER, K
QIAN, XH
HRUBY, VJ
[J]. TETRAHEDRON, 1994, 50 (08) : 2391 - 2404
[6] ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF THE OPTICALLY PURE ISOMERS OF INDOLE-PROTECTED BETA-METHYLTRYPTOPHAN SUITABLE FOR PEPTIDE-SYNTHESIS
BOTEJU, LW
WEGNER, K
HRUBY, VJ
[J]. TETRAHEDRON LETTERS, 1992, 33 (49) : 7491 - 7494
[7] CYCLIC TAUTOMERS OF TRYPTOPHAN - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED AND ALPHA-BETA-DISUBSTITUTED DERIVATIVES OF TRYPTOPHAN
BRUNCKO, M
CRICH, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4239 - 4249
[8] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
BURK, MJ
FEASTER, JE
NUGENT, WA
HARLOW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10125 - 10138
[9] ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
BURK, MJ
GROSS, MF
MARTINEZ, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) : 9375 - 9376
[10] Asymmetric catalytic routes to chiral building blocks of medicinal interest
Burk, MJ
Gross, MF
Harper, TGP
Kalberg, CS
Lee, JR
Martinez, JP
[J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (01) : 37 - 44

← 1 2 3 →